COMPLEMENTS OF ORGANIC CHEMISTRY
Learning outcomes of the course unit
Knowledge and understanding. Aim of the course is to
- acquire knowledge of the structural characteristics, included the stereochemistry, of organic compounds;
- acquire knowledge on the fundamental aspects of thermodynamics and kinetics applied to organic reactions;
- know the nature and behaviour of functional groups in organic compounds;
- know to design a multistep synthesis, including transformation of functional groups, the formation of carbon-carbon and carbon-heteroatom bonds.
Applying knowledge and understanding: in parallel to theoretical explanations, the student will be guided through the resolution of organic chemistry problems. This will also train the student to apply and reinforce the concepts acquired. In particular, the student will be able to:
- carry out simple calculations on energy balance, equilibrium and kinetic constants and to manipulate kinetic equations;
- select the best separation/purification method for a mixture of compounds;
- design a short multistep synthesis to obtain a polyfunctional organic compound being able to evaluate its advantages and drawbacks.
Making judgements: The student will possibly be able to:
- acquire a complete autonomy in the interpretation of the reactivity of organic reactions object of the course;
- collect and critically evaluate the outcome of an experimental data set;
- correlate experimental results with theoretical models.
Communication: at the end of the course, the student will be able to
- properly communicate using the typical terminology of organic chemistry;
- discuss problems of stereochemistry and reactivity of the main classes of the organic compounds object of the course.
Lifelong learning skills. The student will be able to
- start second level university studies with a sufficient degree of independence;
- independently interpret data from the technical-scientific literature especially in a practical field.
Knowledge of Organic Chemistry I and Organic Chemistry II plus basic knowledge of General Chemistry and Physical Chemistry.
Course contents summary
- Organic stereochemistry and methods for the resolution of mixtures of enantiomers
- Oxidation and reduction reagents in organic chemistry
- Aromatic nucleophilic substitution
- Diazonium salts: synthesis and reactivity
- Synthesis of heterocycles
- Special reactions on phenols
- Organometallic reagents in organic chemistry
- Thermodynamics and kinetics in organic chemsitry reactions
- Brief introduction to the retrosynthetic approach
- New synthetic methodologies for drug-discovery
- Aromatic nucleophilic substitution
- Phenols: preparation and reactivity (Friedel-Crafts acylation and alkylation, metal-mediated regioselectivity, Kolbe reaction, Reimer-Tiemann reaction, Fries transposition)
- Heterocyclic synthesis
- Organic stereochemistry. Resolution of racemates: chiral derivatizing agents and kinetic resolution. Stereoselectivity and stereospecificity of the reactions.
- Oxidation and reduction reactions in organic chemistry: chemoselectivity and brief introduction to protecing groups
- C-C bond formation through te use of organometallic reagents
(Grignard reagents, organo-lithium, organo-cuprates, organo-zinc)
- Equilibria, rate of reactions, mechanisms of reactions: Enthalpy and Entropy contributions to organic chemistry reactions, reversible and irreversible reactions, Le Chatelieur-Braun principle, activation energy and kinetics of the reactions, (Rate determining step, 1st and 2nd order reactions), acid and basic catalysis (hydrolysis of esters and amides, isomerisation of alkenes), kinetic and thermodynamic products, reactions at low temperature, role of the solvents.
- Brief introduction to the retrosynthetic approach.
- Innovative synthetic methods for the Drug-design: combinatorial chemistry, parallel synthesis, split-and-mix methods, high-throughput-screening.
J. McMurry - Chimica Organica - Piccin, Padova
J. Clayden, N. Greeves, S. Warren, P. Wothers - Organic Chemistry -
Oford University Press
Brown & Foote - Chimica Organica - EdiSES, Napoli . Paula Yurkanis
Bruice - Chimica Organica - EdiSES,Napoli
Besides the lectures on the more theoretical aspect of the organic reactions and on the thermodynamic and kinetic apsects of organic reactions, a series of problems and exercises will be discussed to foster the students to better understand the concepts and to apply them to practical cases.
The teacher will be available for further explanations and discussions on the argument treated during the course.
The slides using during the course will be available on the web as pdf files.
Assessment methods and criteria
Oral examination will verifying the knowledge of the student through the discussion of organic chemistry problems with the aim to evaluate the ability to apply the competence acquired by the student on the structure and reactivity of organic compounds.
The exam is passed if the student is able to analyse the structure of and organic compound in terms of its reactivity and/or preparation and to discuss the thermodynamic and kinetic issues involved in the reactions. The student's preparation will be verified through the discussion of a problem of organic chemistry reactivity and his ability to apply the knowledge acquired also on the structure-reactivity relationship.
The exam will be passed for students able to autonomously discuss the reactivity of organic reactions (aromatic compounds, heteroaromatics, organometallic reagents, and carbonyl compounds), the transformation of functional groups and the stereochemical issue associated with organic chemistry.
The ability to describe the stereochemistry and the properties of stereoisomers will be also evaluated in details together with the differenet methods for the resoltuion of mixtures of enantiomers (up to further 4 points).
It will be also evaluated the ability to discuss the reactivity of organometallic compounds and the different methods to reduce or oxidize an organic compound (up to further 4 points).
The ability to properly discuss the organic chemistry reaction in terms of kinetics and thermodynamics will allow to gain up to further 4 points.